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Up-Scale Synthesis of p-(CH2=CH)C6H4CH2CH2CH2Cl by CuCN Catalyzed Coupling Reaction of Grignard Reagent with BrCH2CH2CH2Cl
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.advisor | 이분열 | - |
| dc.contributor.author | 박주용 | - |
| dc.date.accessioned | 2025-01-25T01:35:59Z | - |
| dc.date.available | 2025-01-25T01:35:59Z | - |
| dc.date.issued | 2023-02 | - |
| dc.identifier.other | 32595 | - |
| dc.identifier.uri | https://dspace.ajou.ac.kr/handle/2018.oak/24447 | - |
| dc.description | 학위논문(석사)--분자과학기술학과,2023. 2 | - |
| dc.description.tableofcontents | 제 1장 Introduction 1 <br>제 2장 Results and Discussion 2 <br> 1. Catalyst Screening 2 <br> 2. Large-scale synthesis of 1 and 2 5 <br>제 3장 Experimental Section 9 <br> 1. General remarks 9 <br> 2. Catalyst Screening 9 <br> 3. Large-scale synthesis of p-(CH2=CH)C6H4CH2CH2CH2Cl 10 <br> 4. Large-scale synthesis of [p-(CH2=CH)C6H4CH2CH2CH2]2Zn 10 <br> 5. PhCu(CN)Mg(THF)4Cl 11 <br> 6. X-ray crystallography 11 <br>제 4장 Conclusions 12 <br>제 5장 Acknowledgements 13 <br>제 6장 References 13 <br>제 7장 Supporting information 19 | - |
| dc.language.iso | kor | - |
| dc.publisher | The Graduate School, Ajou University | - |
| dc.rights | 아주대학교 논문은 저작권에 의해 보호받습니다. | - |
| dc.title | Up-Scale Synthesis of p-(CH2=CH)C6H4CH2CH2CH2Cl by CuCN Catalyzed Coupling Reaction of Grignard Reagent with BrCH2CH2CH2Cl | - |
| dc.type | Thesis | - |
| dc.contributor.affiliation | 아주대학교 대학원 | - |
| dc.contributor.department | 일반대학원 분자과학기술학과 | - |
| dc.date.awarded | 2023-02 | - |
| dc.description.degree | Master | - |
| dc.identifier.localId | T000000032595 | - |
| dc.identifier.url | https://dcoll.ajou.ac.kr/dcollection/common/orgView/000000032595 | - |
| dc.subject.keyword | CuCN catalyst | - |
| dc.subject.keyword | Grignard reagents | - |
| dc.subject.keyword | PhCu(CN)Mg(THF)4Cl crystal | - |
| dc.subject.keyword | coupling reaction | - |
| dc.subject.keyword | large scale | - |
| dc.description.alternativeAbstract | Grignard reagents featuring carbanion characteristics are generally unreactive toward alkyl halides and require a catalyst for the coupling reaction. With the need to synthesize p-(CH2=CH)C6H4CH2CH2CH2Cl on a large-scale, the coupling reaction of p-(CH2=CH)C6H4MgCl with BrCH2CH2CH2Cl was attempted to screen the catalysts, and CuCN was finally determined to be the best catalyst affording the desired compound in 80% yield with no generation of Wurtz coupling side product CH2=CHC6H4C6H4CH=CH2. The p-(CH2=CH)C6H4Cu(CN)MgCl species was proposed as an intermediate based on the X-ray structure of PhCu(CN)Mg(THF)4Cl. The structures of p-(CH2=CH)C6H4CH2CH2CH2MgCl and p-ClC6H4MgCl were also elucidated, which existed as an aggregate with MgCl2, proposing that some portion of the Grignard reagents were possibly lost in the coupling reaction owing to co-precipitation with the byproduct MgCl2. Using the developed syntheses, [p-(CH2=CH)C6H4CH2CH2CH2]2Zn which is latently useful compound for the production of PS-block-PO-block-PS, respectively, was successfully synthesized with considerable cost reductions. | - |
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- Graduate School of Ajou University > Department of Molecular Science and Technology > 3. Theses(Master)
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